Allyl bromide → 3-Allyloxy-5-hydroxybenzoic acid methyl ester

Methyl 3,5-dihydroxybenzoate (20.9 g, 124 mmol) was dissolved in DMF (30 mL). Potassium carbonate (34.4 g, 249 mmol) was added, followed by allyl bromide (10.5 mL, 124 mmol). The resulting suspension was stirred at room temperature overnight under argon atmosphere. The reaction mixture was quenched with H2O, extracted with EtOAc (2×150 mL). The organic layers were washed with H2O (2×200 mL), dried with MgSO4 and concentrated in vacuo to yield a pale yellow oil which was purified by flash column chromatography eluting with 20% EtOAc in hexane to give a pale yellow solid (10.25 g, 40% yield). 1H NMR (400 MHz, CDCl3) δ 7.08-7.22 (m, 2 H) 6.65 (t, J=2.40 Hz, 1 H) 5.94-6.21 (m, 1 H) 5.73 (s, 1 H) 5.42 (dd, J=17.18, 1.52 Hz, 1 H) 5.31 (dd, J=10.48, 1.39 Hz, 1 H) 4.55 (d, J=5.05 Hz, 2 H) 3.91 (s, 3 H); LCMS for C14H12O4 m/z 209.0 (M+H)+.

1. customThe reaction mixture was quenched with H2O
2. extractionextracted with EtOAc (2×150 mL)
3. washThe organic layers were washed with H2O (2×200 mL)
4. dry with materialdried with MgSO4
5. concentrationconcentrated in vacuo
6. customto yield a pale yellow oil which
7. customwas purified by flash column chromatography
8. washeluting with 20% EtOAc in hexane

ORD record

ord-71638f8d28cc498e84d0504f2fabcc90

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842713B2